
Holiday rentals in Charleston
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Charleston
Guests agree: these stays are highly rated for location, cleanliness and more.

Brickway Retreat
Newly Remodeled 2 Bed, 1.5 Bath home in quiet neighborhood. This modernized house features a large fully furnished kitchen that is open to the dining area. The large living room with 10 ft ceilings has a pull-out sofa. Big screen TVs equipped with Roku streaming service in the master bedroom and living room. Wi Fi throughout the house is included. Enjoy your mornings on the cozy front porch featuring cedar pillars and stamped concrete and enjoy your evenings on the back patio around the fire pit

Craftsman Bungalow Guest House
Welcome to the Craftsman Bungalow Guest House. This special place is close to everything, making it easy to plan your visit. It is a 1930's Sears Craftsman home located near downtown Greenup, about 1 mile from Rt 70. Greenup, known as the Village of the Porches between Interstate 70, IL RT 40 and IL RT 130, with over 1500 residents. Our Main Street (Cumberland St/Il Rt 121) is also part of the National Road, attractive old architecture, beautiful overhanging porches leading to our Covered Bridge

Elk Ridge
Come and enjoy yourself at Elk Ridge, the first B&B of Wildlife Manor! Located within Aikman Wildlife Adventure, we are home to over 240 animals. This retreat offers the scenery of wildlife inside or outdoors. You have the chance to see zebras, bison, camels, and much more! Elk and water buffalo love to take a swim in the pond that Elk Ridge overlooks as well. Enjoy the natural scenery in the evening around a firepit on the waterfront deck. This will be an overnight adventure you won't forget!

The Candy Kitchen
Take a step back in time as you enter this authentic 1930's Soda Fountain located in downtown Greenup Village of the Porches situated on the Historic National Road. The Loomis Family immigrated from Greece and operated the Soda Fountain and Confectionary until the 1960's. It has since been transformed into a spacious and comfortable living area with the original Soda Fountain still intact, beautiful tin ceiling, and also includes a large kitchen, a separate shower room & powder room.

Freshly updated/3 acres/Wildlife/Boat parking
A completely renovated cottage, nestled in the country of Sullivan, just minutes from boating, camping, golf, theatre style shows, and more. If you are looking for peaceful nights, this place is for you! Surrounded by trees and nature where many days you will catch deer roaming the yard. Plenty of yard space for games, a fire table to converse around, and chairs on the porch to sit back, relax, and take in the tranquil sounds that surround you here at Lakewood Cottage.

Wooden Shoe Factory, Historic, w/ Bar & Breakfast
Historic 1880 Wooden Shoe Factory by Wooden Shoe Maker Gerhard Deymann. A great getaway Tiny House from the past with a Bar & Books. Please take some & leave some :-) Fully furnished. Tons of charm. It has a loft, luggage lift, exposed brick/beams, fireplace, bikes, antiques, front sitting area, swing, grill, back patio, yard, private parking, appliances, vaulted ceilings. 6 minutes to I57, I70, Effingham, & dozens of restaurants. 1 block to 7 Teutopolis Bars, & diners.

Sweet Dreams Cabin. Peaceful & Relaxing
Get some quality family time at this newly remodeled cabin near the beautiful Embarrass river. You are surrounded by beautiful woods and a small creek. Lush wildlife is all around you so you can be one with nature. The cabin has all the luxury's to allow for a long term stay as well. Beautiful Lake Charleston is not far away. The large circle drive offers plenty of parking for your boat and guest. The large deck on the rear gives a beautiful view to be enjoyed by all.

The Hideaway - Charming apartment in Arthur IL
Enjoy exploring Illinois' largest Amish settlement while relaxing in this one-bedroom apartment one block from downtown Arthur, a village of 2200. Country charm abounds in this gem which sleeps three (full bed plus fold-out love seat). There is a private entrance, access to laundry facilities, and private parking off the street. We are 9 miles west of I-57 on Route 133 (take exit 203 at Arcola) and 40 miles from Champaign.

Mill Creek Farmhouse
Soon the boats will be cruising across Mill Creek Lake in search of catch of the day or enjoying some water-sports. While you are in the area make plans to stay at the Mill Creek Farmhouse. Enjoy an outdoor fire pit while having the entire house to yourself. In 15 minutes from the driveway you can have your boat launched and then come back to plenty of room for your family to enjoy their evening. Hope to see you soon!

Cottage on Lake Paradise,
Welcome to Paradise Cottage nestled on Lake Paradise! Cozy and warm with wood finishes throughout. Includes three-tiered deck/patio, with the lowest level sitting over the water. Perfect for fishing (this lake hosts an annual fishing tournament), canoeing/kayaking, or just relaxing. Great for bird watching, with great blue herons, egrets, ducks, bald eagles, plovers, cormorants, woodpeckers and other species seen daily.

Sojourners' Abode
Our family has enjoyed good experiences staying at AirBnb houses when traveling, so we decided to provide a place for others coming to our community. Arthur often has lots of activity, but this home away from home will be a peaceful spot for you to unwind. Just half a dozen blocks from downtown, but on a quiet dead end street. Round up a few friends & come enjoy your stay.

The Cozy Stay-Entire Home-Cheerful 3 bedroom home.
Bring the whole family to this great place with lots of room for fun. This house is very kid friendly, and homey with lots of space. 3 Bedrooms, 2 bath, spacious living room, with free parking. The parking is limited to 4 vehicles unless otherwise discussed with the host. Please note all bedrooms are located upstairs!
Popular amenities for Charleston holiday rentals
Other great holiday rentals in Charleston

The Winkleblack

Ultimate Country Home!

Renovated home

Miss Honey’s Cottage

Asa Creek Cottage

Country Living in Mattoon

Shingle Oaks Loft

Wonderland in Paris
Frequently Asked Questions
Are there family-friendly vacation rentals in Charleston?
Charleston has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Charleston?
Experience the best of Charleston with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Charleston?
Yes! Work meets play with ease at over 10 vacation rentals in Charleston featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Charleston have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Charleston. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Charleston have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Charleston. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Charleston have wifi?
Absolutely! We offer over 10 house rentals with wifi in Charleston. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Charleston have free parking?
Absolutely! We offer over 10 house rentals with free parking in Charleston. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Charleston?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Charleston

Total holiday rentals
Explore 20 holiday rentals in Charleston

Nightly prices starting at
Charleston holiday rentals start at € 26 per night before taxes and fees

Verified guest reviews
Over 390 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Charleston holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Charleston rentals

4.9 Average rating
Charleston stays are highly rated by guests – averaging 4.9 out of 5!
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